Biocidal dialkyl (3,5-substituted hydroxyalkyl oxazolidines and hydrocarbylene polyoxymethylene oxazolidines

Abstract

This invention discloses a novel class of hydroxyalkyl oxazolidines, and polyoxymethyleneoxazolidines to be used as bactericides in aqueous surface coating compositions. The compounds have the following structural formulas: ##STR1## wherein R is hydrogen, an alkyl group of 1 to 6 carbon atoms, a cycloalkyl group of 3 to 8 carbon atoms or an aryl group of 6 to 10 carbon atoms; R 1 represents hydrogen, an alkyl group of 1 to 6 carbon atoms, a cycloalkyl group of 3 to 8 carbon atoms, an aryl group of 6 to 10 carbon atoms containing alkyl, halogen, alkoxy, nitro or other substitutuents; R 2 represents hydrogen, an alkyl group of 1 to 6 carbon atoms, a cycloalkyl group of 3 to 8 carbon atoms, or an aryl group of 6 to 10 carbon atoms; and n represents an integer in the range of 0 to 8.

We claim: 
     
       1. A method for inhibiting bacterial growth in aqueous surface coating compositions which comprises treating the composition with a bactericidally effective amount of a polyoxymethyleneoxazolidine having a structural formula: ##STR6## wherein R is an alkyl group of 1 to 6 carbon atoms, a cycloalkyl group of 3 to 8 carbon atoms or an aryl group of 6 to 10 carbon atoms; R 1  represents a hydrogen, an alkyl group of 1 to 6 carbon atoms, a cycloalkyl group of 3 to 8 carbon atoms, an aryl group of 6 to 10 carbon atoms, a substituted aryl group of 6 to 10 carbon atoms having alkyl, halogen, alkoxy, or nitro substituents; R 2  represents an alkyl group of 1 to 6 carbon atoms, a cycloalkyl group of 3 to 8 carbon atoms, or an aryl group of 6 to 10 carbon atoms; and n represents an integer in the range of 1 to 8. 
     
     
       2. The method according to claim 1, wherein the concentration of the bactericide in the aqueous surface coating composition is in the range of 0.005% to 1.0%. 
     
     
       3. The method according to claim 1, wherein the polyoxymethyleneoxazolidine is 3-(2-hydroxymethyleneoxy)propyl-5-methyloxazolidine. 
     
     
       4. The method according to claim 1, wherein the polyoxymethyleneoxazolidine is 3-[2-(hydroxymethyloxymethyleneoxy)]propyl-5-methyloxazolidine. 
     
     
       5. The method according to claim 1, wherein the polyoxymethyleneoxazolidine is 3-[2-(hydroxymethyl-di(oxymethylene)oxy]propyl-5-methyloxazolidine. 
     
     
       6. The method according to claim 1, wherein the polyoxymethyleneoxazolidine is 3-[2-(hydroxymethyl-tri(oxymethylene)oxy]propyl-5-methyloxazolidine. 
     
     
       7. The method according to claim 1, wherein the polyoxymethyleneoxazolidine is 3-[2-(hydroxymethyl-tetra(oxymethylene)oxy]propyl-5-methyloxazolidine. 
     
     
       8. An aqueous biocidal composition useful to inhibit the growth of bacteria, without inhibiting fringe at 125 ppm or below, in aqueous surface coating compositions comprising a bactericidal polyoxymethyleneoxazolidine having a structural formula: wherein R is an alkyl group of 1 to 6 carbon atoms, a cycloalkyl group of 3 to 8 carbon atoms or an aryl group of 6 to 10 carbon atoms; R 1  represents a hydrogen, an alkyl group of 1 to 6 carbon atoms, a cycloalkyl group of 3 to 8 carbon atoms, an aryl group of 6 to 10 carbon atoms, a substituted aryl group of 6 to 10 carbon atoms having alkyl, halogen, alkoxy, or nitro substituents; R 2  represents an alkyl group of 1 to 6 carbon atoms, a cycloalkyl group of 3 to 8 carbon atoms, or an aryl group of 6 to 10 carbon atoms; and n represents an integer in the range of 1 to 8, which aqueous biocidal composition, upon dilution into aqueous surface coating compositions, yields a concentration of the polyoxymethyleneoxazolidine in the aqueous surface coating compositions of at least 0.005% by weight.   
     
     
       9. The aqueous biocidal composition according to claim 8 wherein the polyoxymethyleneoxazolidine is 3-(2-hydroxymethyleneoxy)propyl-5-methyloxazolidine. 
     
     
       10. The aqueous biocidal composition according to claim 8 wherein the polyoxymethyleneoxazolidine is 3-[2-(hydroxymethyloxymethyleneoxy)]propyl-5-methyloxazolidine. 
     
     
       11. The aqueous biocidal composition according to claim 8 wherein the polyoxymethyleneoxazolidine is 3-[2-(hydroxymethyl-di(oxymethylene)oxy]propyl-5-methyloxazolidine. 
     
     
       12. The aqeuous biocidal composition according to claim 8 wherein the polyoxymethyleneoxazolidine is 3-[2-hydroxymethyl-tri(oxymethylene)oxy]propyl-5-methyloxazolidine. 
     
     
       13. The aqueous biocidal composition according to claim 8 wherein the polyoxymethyleneoxazolidine is 3-[2-(hydroxymethyl-tetra(oxymethylene)oxy]propyl-5-methyloxazolidine. 
     
     
       14. The aqueous biocidal composition according to claim 8 wherein the concentration of polyoxymethyleneoxazolidine in aqueous solution is 50%.